Drake's Five Saddest Miami Moments

Drake is perhaps the only rapper on this planet who walks such a thin line between cool and sad. Often, sometimes within the same song, he'll brag equal parts about bedding women and getting his heart broken by them.

Drake was sporting a haircut that could have been carved only by an evil barber.

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When cracking open a new Drizzy album, there's always a moment before the beat drops when it's unclear whether you're about to listen to four minutes of a friend gloating about who he banged last night or four minutes of a friend crying over that one time in high school when he went to go check on his prom date, who had been in the bathroom for, like, 30 minutes, only to find her tongue down Patrick O'Donoghue's throat.

One of Drake's favorite places in this country is Miami. He has named-dropped the city in song after song, he celebrated New Year's Eve in the 305 last year, and he'll throw two back-to-back concerts at the American Airlines Arena on August 30 and 31 (followed by two back-to-back afterparties at E11even). But it hasn't all been strippers and champagne for the 6 God when it comes to the Magic City. Though Drake's finally embraced his role as America's coolest uncool rapper — which has helped make him even cooler (it's confusing; we know) — there was a time when everything Drake did just was sort of, well, depressing. 

Here are just a few of Drake's saddest Miami moments.

5. The entirety of the "I'm on One" music video.

Drake has been part of some pretty epic and decidedly un-sad music videos, like "Hotline Bling." Remember that one? He wore a turtleneck sweater and danced like a Thanksgiving turkey that had just been pardoned by the president, and still — somehow — it was awesome. But before those days, Drake was the centerpiece of one of the saddest music videos to ever come out of Miami. It was for the DJ Khaled track "I'm on One," with Rick Ross and Lil Wayne, and it was a master class in melancholy. Poor Drake. The video was actually filmed in his unfurnished Miami apartment. His friends sat on furniture covered in plastic and wore expressions that looked like all of their moms just yelled at them on speakerphone. Drake sported a haircut that could have been carved only by an evil barber, and he wore one of those polo shirts where the Polo logo is way too big and looks like an actual jockey is resting on his boob. Also, DJ Khaled was drinking a can of Four Loko, which is scientifically proven to be very bad for your health, and anything that brings DJ Khaled closer to death is the saddest thing in the universe. The one silver lining of the video is that Rick Ross is still fat. Man, I miss fat Rick Ross.

4. When he went to Tootsie's, but all he wanted was a "shoulder rub."

One of Drake's most iconic tracks came in the form of his "Back to Back" freestyle, a knockout blow in an ongoing feud with Philly rapper Meek Mill. It was an epic comeback and one of the most decisive wins in hip-hop-beef history. It was the rap equivalent of those intensely satisfying YouTube videos that show the moment when the scrawny kid snaps and proceeds to unleash his years' worth of middle-school rage by pile-driving a bully into a water fountain. Still, even in this epic dis track, Drake sneaks in one of his saddest lyrics ever: "I mean whoa, can't fool the city, man, they know what's up/Second floor at Tootsie's, getting shoulder rubs." Though there was a bit of controversy as to whether Drake was name-dropping Tootsie's the Miami strip club or Ms. Tootsie's the popular Philadelphia soul-food restaurant, we're going to go with the Miami Tootsie's, because soul-food restaurants don't typically include a Swedish massage with their chicken wings. So let that sink in for a moment. Drake went to Tootsie's, one of the wildest strip clubs in Miami, and all he wanted to do was sit in silent reflection while a woman named Sapphire soothingly rubbed his shoulders.

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Ryan Pfeffer is a contributor and former Miami New Times music editor. After earning a BS from Florida State University, Ryan joined the New Times staff in November 2013 as a web editor.
Contact: Ryan Pfeffer